(2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester
• CAS No.: 119794-83-1
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.373

Synonyms:(2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester

Chemical Property of (2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester

There total 27 articles about (2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tert-butyl 6-O-(tert-butyldimethylsilyl)-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose (119794-57-9) → (2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester (119794-83-1)

Guidance literature:

Multi-step reaction with 12 steps

1: Irradiation

2: pyridine / CH₂Cl₂

3: 94 percent / t-BuOH / tetrahydrofuran / 1.) from -78 deg C to 0 deg C, 2.) -78 deg C

4: 94 percent / diethyl ether

5: 86 percent / SOCl₂, pyridine

6: H₂ / Raney Ni / methanol

7: methanol

8: 84 percent / DIBAL / CH₂Cl₂ / -78 °C

9: 81 percent / n-Bu₄NF / tetrahydrofuran

10: 88 percent / 1.) Ph₃P, I₂, imidazole / tetrahydrofuran; benzene

11: 92 percent / Bu₃SnH, AIBN / benzene / Heating

12: 12 M HCl / tetrahydrofuran

With pyridine; 1H-imidazole; hydrogenchloride; thionyl chloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triphenylphosphine; tert-butyl alcohol; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00244a061

Reference yield:

tert-butyl 6-O-(tert-butyldimethylsilyl)-3,4-dideoxy-4-C-<(trimethylacetoxy)methyl>-α-D-erythro-hexopyranosid-2-ulose (114094-16-5) → (2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester (119794-83-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / t-BuOH / tetrahydrofuran / 1.) from -78 deg C to 0 deg C, 2.) -78 deg C

2: 94 percent / diethyl ether

3: 86 percent / SOCl₂, pyridine

4: H₂ / Raney Ni / methanol

5: methanol

6: 84 percent / DIBAL / CH₂Cl₂ / -78 °C

7: 81 percent / n-Bu₄NF / tetrahydrofuran

8: 88 percent / 1.) Ph₃P, I₂, imidazole / tetrahydrofuran; benzene

9: 92 percent / Bu₃SnH, AIBN / benzene / Heating

10: 12 M HCl / tetrahydrofuran

With pyridine; 1H-imidazole; hydrogenchloride; thionyl chloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triphenylphosphine; tert-butyl alcohol; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo00244a061

Reference yield:

tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-2,3,4-trideoxy-4-C-<(trimethylacetoxy)methyl>-2-C-methylene-α-D-arabino-hexopyranoside (114094-38-1) → (2R,3S,4R,5R)-4-Benzyloxycarbonylamino-6-hydroxy-2,5-dimethyl-tetrahydro-pyran-3-carboxylic acid methyl ester (119794-83-1)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Raney Ni / methanol

2: methanol

3: 84 percent / DIBAL / CH₂Cl₂ / -78 °C

4: 81 percent / n-Bu₄NF / tetrahydrofuran

5: 88 percent / 1.) Ph₃P, I₂, imidazole / tetrahydrofuran; benzene

6: 92 percent / Bu₃SnH, AIBN / benzene / Heating

7: 12 M HCl / tetrahydrofuran

With 1H-imidazole; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triphenylphosphine; nickel; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00244a061

upstream raw materials:

tert-butyl 3-(carbobenzyloxyamino)-4-C-carbomethoxy-2,3,4,6-tetradeoxy-2-C-methyl-α-D-glucopyranoside

tert-butyl 6-O-(tert-butyldimethylsilyl)-3,4-dideoxy-α-D-glycero-hex-3-enopyranosid-2-ulose

2,2-Dimethyl-propionic acid (2S,3R,4S,6R)-4-amino-6-tert-butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-pyran-3-ylmethyl ester

tert-butyl 6-O-(tert-butyldimethylsilyl)-3,4-dideoxy-4-C-<(trimethylacetoxy)methyl>-α-D-erythro-hexopyranosid-2-ulose

Downstream raw materials:

(3R,4R,5S,6R)-4-benzyloxycarbonylamino-3,4,5,6-tetrahydro-5-methoxycarbonyl-3,6-dimethyl-2H-pyran-2-one

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